Quinin ester.



"onrrnn sra rns PATENT onnron.

HEINRICH THRON, OF FRANKEORT-ON-THE-IVIAIN, GERMANY, ASSIGNOR T0 VEREIN- IGTE CHININFABRIKEN ZIMMER & 00., G. 1Vf. B. XL, 03? FRANKIEORT-ON-THE-MAIN,

GERMANY, A SOCIETY or GERMANY.

QUININ ESTER.

No Drawing.

Specification of Letters Patent.

Patented Dec. 13, 1910.

Application filed March 30, 1910. Serial No. 552,369.

To all whom it may concern:

Be it known that I, I-IETNRIGH THRON, a sub ect of the German Emperor, and resident of Frankfort-on-the-Main, Germany, have organic acid esters of the hydrohalogenic addition products of quinin by coupling together hydrohalogenic acids with the organic acid. esters of quinin, and the new products obtained thereby. These products are useful. because their hydrohalogenic acid is bound in an intramolecular way, so that they combine with the action of the quinin the action of their halogen, and because they are tasteless. The said coupling together may be carried out in practice in various ways, as shown by the following examples.

Example 1. d1 alclag of lig clroclzlcrguinln ethyl carbonic acicl csicrs.3.605 kilograms of hydrochlorquinin (1 11101.) are mixed with 20 kilograms of benzene, 1.085 kilograms of chlor-formic ethyl-ester (1 mol.) are added, whereupon the whole is heated a short time at boilingtemperature. After cooling the product is extracted by means of hydrochloric acid, precipitated with ammonia and crystallized out of diluted alcohol. The reaction takes place according to the following equation:

(I-Iydrochloroquinin) was 8.2 per cent.

Emamplc 2. Making of h z clrocltlorlsoqnlnln ethyl carbonic acid ester. 3.605 kilograms of 11ydrochlorisoquinin (1 11101.) are dissolved in 20 kilograms of benzene, 0.79 kilograms of pyridin (1 mol.) are added, 1.085 kilograms of chloroformicethylester (1 mol.) are slowly added to the-solution, and finally the solution is heated to boiling temperature. The hydrochlorisoquinin employed in this process is represented by the formula ao an z z and consists of fine colorless crystal needles, has an intensiye bitter taste, is easily soluble in alcohol, ether and chloroform and hardly soluble in petrol-benzin. Its melting point is 183 centigrade. The hydrochlorisoqui nin-ethylcarbonate which is thus obtained is extracted by means of diluted hydrochloric acid. precipitated by ammonia, and crystallized from five times the amount of alcohol. The reaction takes place according to the following equation:

(Hydrochlorisoquinin) 0,,H,,N,O,C1+C1.000.0,H,:

o rr mo,crooooan gaor Thereby large, colorless and tasteless prisms are obtained which melt at a temperature offrom 191 to 192 degrees centigrade, which are easily soluble in benzene, aceton, chloroform, and hot alcohol, but insoluble in petroleum-benzin and water. The diluted solution in sulfuric acid shows a green fluorescence. Hydrochlorisoquininethylcarbonat is soluble in diluted acids, and is precipitated from such solutions by alkalies. The analysis showed 8.33 per cent. of chlorin. The result of the calculation from C H N,O,CLCOOC,H 

